Ethylene Glycol → 2-[3-(2-Chloroethoxy)-4-nitrophenoxy]ethanol

HRID 2219012Notes

Reaction equation

HRID 2219012 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13].[OH:15][CH2:16][CH2:17][OH:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])[O:15][CH2:16][CH2:17][OH:18]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 10796Cesium carbonateHCID 431355982-(2-Chloroethoxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 597713092-[3-(2-Chloroethoxy)-4-nitrophenoxy]ethanolYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-chloroethoxy)-4-fluoro-1-nitro-benzene (91.3 g, 6 mmoles), 2-hydroxyethanol (0.57 g, 7.2 mmoles), and cesium carbonate (2.34 g, 7.2 mmoles) in DMF were stirred together at room temperature for 1 hour, diluted with water and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound (0.63 g, 2.4 mmoles), identified by HNMR and mass spectral analyses.

Workup

  1. extractionextracted with EtOAc
  2. washwashed sequentially with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-485b619ba8dd47ac817680017c9b486c
Source dataset
uspto-grants-2008_08
Patent number
US07414051B2

Reaction notes

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